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It was Frederick Hutson’s first ride on “Con Air.” He boarded in Las Vegas while pondering what awaited him at trial in Florida, where he had been shipping hundreds of pounds of marijuana for the past four years. It was October 2007, and Hutson had just been indicted along with 10 comrades after a year-long federal investigation. He shuffled onto the plane shackled at his hands and feet, chained to other prisoners. An older inmate asked Hutson about his case, and shared one piece of advice: “Make sure to ask your lawyer to do the safety valve.” So when his public defender advised him to take a plea deal for 10 years of prison time or face 30 years if he lost at trial, Hutson asked about it.

Frederick Hutson

“He had never mentioned it the whole time,” Hutson says, “He looks at me crazy, and he says, ‘Yeah, you do qualify for the safety valve.’” The safety valve allows federal judges to break from mandatory sentences if it’s a nonviolent crime, the offender cooperates with authorities and has no previous criminal history. Hutson took the deal, and the judge cut the sentence to 51 months.

“This is partly why our business works so well,” Hutson says, sitting in his Downtown Las Vegas office. “Because there is no information on the prison system until you are actually in it. There’s no way for people outside to understand how it works.”

That business is Pigeonly, a growing set of services that helps prisoners and their friends and family keep in touch with photos and phone calls. Without the safety valve, Hutson would still be in prison, and the Silicon Valley venture capitalists who have backed Pigeonly with $3 million would be investing their money elsewhere.

Hutson, 30, has always been a problem solver. At 13, after his parents divorced and his mother moved him from Brooklyn to St. Petersburg, Florida, he started making money knocking on doors in their 15-story high rise to see if neighbors needed small repairs. He was an average student, bored by textbooks, but he loved getting his hands on things to figure out how they worked. “I was always tinkering with things and taking stuff apart trying to put it back together and make something new,” he says.

After graduating from high school, Hutson joined the Air Force at 19. He was sent to Nellis Air Force Base, where he was an electrician on the F-16s. But Hutson wanted his own business, so he bought a window-tinting shop, working days at the store and nights on base.

By then his high schools friends in Florida were involved in running marijuana coming in from Mexico across the United States. Some stayed with Hutson while in Las Vegas, and mentioned driving huge shipments cross-country. Hutson’s problem-solving nature kicked in, and he couldn’t resist trying to make the network better.

He started shipping the marijuana through services like UPS, first by having partners sit on unaffiliated houses and grab the packages when they were dropped off. Later, he directly paid off the truck drivers. Hutson says he was never pressured to join in. He saw a logistics problem and wanted to fix it, and then there was money to be made. He naively thought he would only get a “slap on the wrist.”

“I think the same thing that makes me a good entrepreneur now is the same thing that had my judgment clouded then,” he says. “Basically, in order to be a good entrepreneur you are constantly being optimistic and positive and almost lying to yourself. You have to be able to get up every day and go to work and try to build something where everything in nature and the world around you is going to resist, especially if you are trying to build something disruptive.”

In 2006, when the Air Force was downsizing, Hutson volunteered for honorable discharge and placement on inactive duty. The trafficking business was rolling, and he was routinely flying with stacks of cash in his backpack. He even used it to buy an A-OK Mail Center on East Charleston, making it that much easier to package, send and track shipments.

The authorities caught wind of the operation when one of the drivers got busted in Arizona. On February 4, 2007, on Hutson’s way back to Las Vegas, federal agents stopped him at the Tampa International Airport, confiscating $39,450 before releasing him. “At that point I knew something was coming, but the bottom had already blew up,” he says. “So, I was just waiting to see how much damage it would be at that point.”

Seven months later, ICE and the DEA raided his mail center.

Hutson was arrested and charged with criminal conspiracy to distribute more than 1,000 kg (about 1 ton) of marijuana. The other members of the drug ring were listed in the indictment, with Hollywood-worthy nicknames like “Trigger,” “Dolla” and “Dread.” Next to Hutson’s name, the indictment read: “aka Fred.”

“Fred” is what everyone at Pigeonly calls him. There are 16 employees, most working out of a two-story apartment Downtown. It has a distinct startup feel, with brainstorming sessions chronicled on the white walls in scrawls of dry-erase marker and a “crash pad” for visiting investors.

“The whole time I’m in prison I’m thinking about what I’m going to do when I’m released,” Hutson says. “I wasn’t going to leave it to someone offering me a job. I knew I’d be competing with people who would have college degrees and don’t have criminal records.”

He created five or six business plans, including one drawing directly on his experience in prison. “When I wrote the business plan for Fotopigeon, it was frustrating to me how hard it was for people on the outside to send me photos,” he says of the service that became the foundation of Pigeonly. “It was frustrating to me how hard it was and expensive it was for me to keep in touch. It was excruciatingly difficult.”

Some of the difficulty stemmed from the fact that Hutson served time in four different prisons during his sentence. And thanks to a federal policy that places inmates within 500 miles of their previous address (considered a kindness), he was incarcerated in California and Arizona instead of near his family in Florida.

When he was released to a Florida halfway house he contacted an Air Force buddy, Alfonzo Brooks, who had sent letters to Hutson in jail only to see them returned because he could never track down the right address. Brooks, now Pigeonly’s chief operating officer, agreed to hire Hutson so he could work on the business.

Its core service is a database they built that allows customers to find federal prisoners in penitentiaries across the country. Then, through their smartphones or computers, they can send printed photos to the prisoner through Fotopigeon, or use Telepigeon, a cheap long-distance call service—something that can be exorbitantly expensive in prison, to the point where some inmates might forego connecting with loved ones.

There are 2.3 million prisoners in the U.S., and even more friends and family who want to stay in touch. Besides the potential of the untapped market, Hutson sees an opportunity to cut down on repeat offenders. Research consistently shows that communication with the outside world helps prisoners stay out of trouble when they are released.

Hutson moved Pigeonly to Las Vegas after participating in a program for out-of-the-box tech entrepreneurs in San Francisco called NewME.

“Frederick is very analytical, and that comes in handy when he needs to be honest and critical of himself and his own business,” says Angela Benton, founder of NewME, which has a 4 percent stake in Pigeonly. “He is a very hard worker. He is someone who is extremely focused and does what he needs to do to be successful.”

Benton advised Hutson to embrace his past, positioning him as an expert. Still, some investors cringed at the notion of backing an ex-con. Of the first 60 he pitched, six wrote checks. One of those was Mitch Kapor, whose investment firm targets businesses with a social mission.

“Frederick had one of the strongest initial presentations I’ve seen,” says Kapor, whose company invested $350,000 in Pigeonly. “And his experience is what gave credibility to the idea. This is an underserved market and an opportunity to find a fresh approach inspired by e-commerce.”

Hutson and Pigeonly exemplify the need for Silicon Valley to look outside traditional areas for entrepreneurial talent, Kapor says. “This is an instance where looking more broadly helps you see that there are needs and therefore opportunities all over the place. Founders come from a wide variety of backgrounds, and entrepreneurs with different lived experiences will see different problems and create solutions to those problems.”

Hutson is sharing the opportunity. Several members of his team have felony records. “When you check the box ‘have you ever been convicted of a crime,’ it’s a plus here ... your file goes to the top of the pile,” Hutson says. “Most people when they get out of prison, they want to turn their life around. Most people don’t think they have things available to them so they don’t even bother knocking on the door. If you give someone an opportunity, and they feel like it’s something they can do, they go for it.”